In it, he talks about how Jobs asked him to design three different kinds of prototypes for the Macintosh.

One group would be prototypes that looked like "what sony would do if it built computers."

The second would be "Americana" design – "reconnecting high-tech design with classical american design statements, especially raymond loewy's streamlined designs for studebaker and other automotive clients, the electrolux line ofhousehold appliances, gestetner's office products, and (naturally), the coke bottle."

For the third group, Jobs gave Esslinger free reign to "be as radical as possible."

As you can probably guess if you are familiar with Macs from the 1980s, the third design group won-out in the end.

It's funny: looking at pictures from that "radical" group, the designs look the least radical today. That's probably because Essingler's Macintosh design was so highly regarded and quoted so endlessly that it has been normalized.

Here's another image from that line that looks a little stranger to modern eyes:

A final thought: Doesn't the Americana design look a lot like where Apple design went toward the turn of the century, first with the unibody iMacs and later with the white iBooks and iPods?